10 tools, 15 Slack channels, very few deals

Hey friends,

Today I want to talk about what really happens when early-stage startups start scaling their sales team.

I love working from the beginning (a few hundred closed-won deals) because I can control the phase I’m talking about today.

But sometimes I start working with founders past a certain scale: €500K, €1M, €2M, sometimes even €5M ARR.

And what I find is most of the time: confusion.

Too many shiny objects:

• GTM engineers
• SDRs vs AEs ratio all over the place
• Multiple tools and softwares
• Slack channels with agents in it
• Workflows.

All noise.

Despite all this, deals are little. Closings are below 20% win rate. CRM is a mess. Team is overwhelmed.

Moreover - which is maybe the most serious thing- nobody’s really watching what’s happening.

No accountability. Nobody listens to demos or gives feedback.

Nobody checks if the playbook is even being used or if the CRM is up to date.

When I step in, first thing I do is hit pause on everything.

Because you can’t go fast if you are over-structuring your GTM motion.

What I see when I open the CRM

Lots of signals. Lots of noise - very few deals in the pipeline.

It usually looks like one of these:

• Lots of discovery calls, and no demos.
• Lots of demos, and no closing.
• Many lists and sequences, and nobody knows which ones bring meetings.

Early stages (new, discovery, demo) jammed, later stages (proposal, contracts, won) are almost empty.

The team is busy. Everyone’s working hard.

They’ve been grinding for months. But nobody can tell me where the next deal is coming from. Or why we closed last one.

Nobody looks at the dirty (important) stuff.

What’s always missing? Accountability.

It’s all GTM, automation, workflows. Less human, more tech. And nobody touches the things that actually needs to be touched:

• Nobody listens to the calls and the demos.
• Nobody gives feedback to the reps.
• Nobody opens the stuck deals and asks why they are stuck.

Everyone’s obsessed with the shiny stuff, but nobody checks if any of it actually brings deals.

Attribution is all over the place, spend is out of control.

This is a massive mistake.

Sales is simple

For me, sales at this stage is three things:

1. Create pipeline, every week.
2. Move pipeline, fast.
3. Close pipeline.

That’s it.

When I step in, everything we build has to push one of these three. If not, we cut it.

In practice, it looks like this:

• One lean outbound process: Everyone does it. AEs take the big accounts, the rest go to the team. Cold calling, social selling, with 1:1 personalised outreach preferred to spray and pray all the times.
• One strong discovery call playbook: whatever you are doing, you are doing it wrong if you are not running A-tier discovery calls. BANT, MEDDIC, MEDDPICC. Pick whatever qualification method you like, as long as everybody uses the same one on every deal.
• A clear demo process: The demo always ties back to discovery. Whoever did the discovery hands over what they learned, and the demo only covers the client’s real problems. Nothing else.
• Accountability & continuous coaching: Every week, someone listens to calls, gives feedback, reviews follow-ups, and digs into stuck deals.

That’s the whole setup: one page, max.

About the tools

Signals are fine. Enrichment is fine. But you don’t need a big machine for any of it.

Today I do most of this with Claude Code, Apollo and a couple of tools that give me a clean list of people to reach out to.

If you want to enrich with Clay or something else, you can do that too.

But my view never changes.

Whatever you think your sales setup needs, cut the complexity in half. Then cut it again.

You won't need the complex setup at this stage, there will be a time (later) when these things will help, just not right now.

Thanks for reading this far; see you all next week!

– Matteo

‍